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Suggested Trip Plan

Browse All Trip Plans
The Berkshires, Massachusetts

The Berkshires, Massachusetts for Babies

3 day trip

Day 1

    • Amusement Park
    • Water Park
    Six Flags New England

    Agawam, MA

    Look, up in the sky! It's a bird! It's a plane! No, it's a car full of riders screaming their lungs out as they speed down a 221-foot drop at 77 miles per hour! ...

    • Take-Out
    • American
    • Burgers
    • Family Dining
    Dakota Steak House

    Pittsfield, MA

    Ask for a family friendly place and locals will lead you here. The busy, log-cabin style eatery appeals to kids, with its hunting-lodge décor, extensive children's menu, overflowing plates, and a fabled Mud Pie for dessert. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

Day 2

    • Special Collection
    • Historical Landmark
    • Roadside Landmark
    • Train
    Berkshire Scenic Railway Museum

    Lenox, MA

    Scenic rides aboard this mobile museum are in vintage 1920s cars, pulled behind a diesel engine run by an overalls-clad engineer. Excursions are the perfect length for little riders—about 30 minutes to Stockbridge, with a quick stop midway in Lee....

    • Art Museum
    • History Museum
    • Science & Nature Museum
    • Special Collection
    • Historical Landmark
    • Aquarium
    • Theater
    Berkshire Museum

    Pittsfield, MA

    Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....

    • Italian
    • Café
    • Take-Out
    Café Lucia

    Lenox, MA

    Families like this friendly "bit of Italy in the Berkshires" for its outdoor seating (in season) and the fresh food. Parents like its local flavor, and although it doesn't have a kids menu, staff will happily adapt dishes to suit kid tastes....

    • Historical Landmark
    • Live Music Venue
    Tanglewood

    Lenox, MA

    The picnickers start arriving an hour ahead of time, unpacking ginormous spreads with tablecloths, silverware, even candelabras (really!). Such elaborate concert-night dining is a tradition here, and it's a hoot to be part of. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

Day 3

    • History Museum
    • Historical Landmark
    Hancock Shaker Village

    Pittsfield, MA

    If not for the cars buzzing by on Route 20, you'd think you'd stepped into a completely different era. Ye Olde Village has vintage buildings showing how the Shakers used to sleep, eat, and do other things. ...

    • Art Museum
    • Special Collection
    Norman Rockwell Museum

    Stockbridge, MA

    Paintings at this charming museum aren't just art: they're stories. Familiar even to kids, Rockwell is a perfect introduction to painting. The artist's intricately crafted details make viewing feel like you're peering through the window of a dollhouse. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

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Suggested Trip Plan

Browse All Trip Plans
The Berkshires, Massachusetts

The Berkshires, Massachusetts for Babies

3 day trip

Day 1

    • Amusement Park
    • Water Park
    Six Flags New England

    Agawam, MA

    Look, up in the sky! It's a bird! It's a plane! No, it's a car full of riders screaming their lungs out as they speed down a 221-foot drop at 77 miles per hour! ...

    • Take-Out
    • American
    • Burgers
    • Family Dining
    Dakota Steak House

    Pittsfield, MA

    Ask for a family friendly place and locals will lead you here. The busy, log-cabin style eatery appeals to kids, with its hunting-lodge décor, extensive children's menu, overflowing plates, and a fabled Mud Pie for dessert. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

Day 2

    • Special Collection
    • Historical Landmark
    • Roadside Landmark
    • Train
    Berkshire Scenic Railway Museum

    Lenox, MA

    Scenic rides aboard this mobile museum are in vintage 1920s cars, pulled behind a diesel engine run by an overalls-clad engineer. Excursions are the perfect length for little riders—about 30 minutes to Stockbridge, with a quick stop midway in Lee....

    • Art Museum
    • History Museum
    • Science & Nature Museum
    • Special Collection
    • Historical Landmark
    • Aquarium
    • Theater
    Berkshire Museum

    Pittsfield, MA

    Kids love the "magic" entryway (doors open outward by themselves) and just about everything else at this landmark science-meets-history-meets-art kids' museum. Surprises are everywhere....

    • Italian
    • Café
    • Take-Out
    Café Lucia

    Lenox, MA

    Families like this friendly "bit of Italy in the Berkshires" for its outdoor seating (in season) and the fresh food. Parents like its local flavor, and although it doesn't have a kids menu, staff will happily adapt dishes to suit kid tastes....

    • Historical Landmark
    • Live Music Venue
    Tanglewood

    Lenox, MA

    The picnickers start arriving an hour ahead of time, unpacking ginormous spreads with tablecloths, silverware, even candelabras (really!). Such elaborate concert-night dining is a tradition here, and it's a hoot to be part of. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

Day 3

    • History Museum
    • Historical Landmark
    Hancock Shaker Village

    Pittsfield, MA

    If not for the cars buzzing by on Route 20, you'd think you'd stepped into a completely different era. Ye Olde Village has vintage buildings showing how the Shakers used to sleep, eat, and do other things. ...

    • Art Museum
    • Special Collection
    Norman Rockwell Museum

    Stockbridge, MA

    Paintings at this charming museum aren't just art: they're stories. Familiar even to kids, Rockwell is a perfect introduction to painting. The artist's intricately crafted details make viewing feel like you're peering through the window of a dollhouse. ...

    • Hotel / Motel
    Red Lion Inn

    Stockbridge, MA

    Stay here for the lovely rooms and the vintage feel. The old stagecoach stop breathes history, from the lovely tea parlor to the old cage elevator (kids can actually ride it—just ask) to the grandfather clock that chimes on the hour. ...

300x250